Surprising interview questions you just might face

Even the most prepared candidates can get stumped during the interview process. After all, while you may have canned answers for the dreaded “What’s your weakness?” and “Where do you see yourself in five years?” queries, are you ready to tell a potential boss about your relationship with your mother or your policy on tipping at a restaurant?

We checked in with eight top execs from around the country to find out the questions they most like to ask candidates and why. Some are wacky. Some are refreshing. But all should be things you can answer without thinking twice.

Favorite question: “We all have to break the rules sometimes. Tell me about a time you had to do so, and how did it turn out?”

Reason for asking: “Your response speaks volumes about your capacity for risk or your willingness to question assumptions. The best candidates have described covering for a staff member who needed to take care of a sick child or sharing a private business strategy with a trusted client. I watch for people who take the question in stride, ponder a moment and then describe a time when they made things better by showing flexibility and innovation.”

Lauren Clifford Knudsen, vice president of J Public Relations (New York City)

Reason for asking: “Our industry relies on media. I ask this question to get a better sense of who a person is beyond professional interests. Their selection can show a love for cooking or fitness, or if they’re more liberal or conservative.”

David Daneshgar, cofounder of BloomNation.com, a marketplace for florists (Santa Monica, California)

Favorite question: “What would you tip on a $335 bill? Can you talk out how you got your answer?”

Reason for asking: “From my experience, those who can do math in their head and on the spot end up being some of the best people in sales, development and support.”

Liliane Stransky, president and founder of Step by Step Foundation, a nonprofit that helps underprivileged children (Miami)

Favorite question: “How would you handle a potentially dangerous situation?”

Reason for asking: “I want to know that my employees are ready to take control of a situation without panicking, and that they can help everyone feel comfortable, safe and secure.”

Reason for asking: “It helps me to understand someone’s work ethic. I have received answers from ‘Well... what are your hours?’ (obviously, not a winning candidate) to ‘Once I get through my entire to-do list and have checked in with other teammates to see if there is something I can help them complete for the day.’ The answer to this question is very telling about whether someone works in a vacuum, is a clock watcher or considers herself to be a person who pitches in.”

Deborah Osburn, founder and creative director of the tile company Clé (Sausalito, California)

Favorite question: “Name a time when you felt overwhelmed by a task.”

Reason for asking: “Artists are inventors, so the responses here can be very telling. I need to see that a candidate can persevere.”

George Gonzalez, owner of George The Salon (Chicago)

Favorite question: “Tell me about your family.”

Reason for asking: “The work culture I’m trying to create is best for people with a strong sense of family. Work is a type of family, after all.”